N'-cyano(2,6-dimethylphenoxy)imidocarbonyl azide | 121868-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-cyano(2,6-dimethylphenoxy)imidocarbonyl azide
• 英文别名: N'-cyano(2,6-dimethylphenoxy)carbimidoyl azide；(2,6-dimethylphenyl) N'-cyano-N-diazocarbamimidate
• CAS: 121868-38-0
• 化学式: C₁₀H₉N₅O
• 分子量: 215.214
• InChiKey: MYDDOKQSUYTMOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  降冰片烯 、 N'-cyano(2,6-dimethylphenoxy)imidocarbonyl azide 以 二氯甲烷 为溶剂， 反应 2.0h， 以82.5%的产率得到exo-3-(N'-cyano(2,6-dimethylphenoxy)carbimidoyl)-3-azatricyclo<3.2.1.02,4>octane
  参考文献：
  名称：

  Functionalization of olefins by alkoximidoylnitrenes

  摘要：

  DOI：

  10.1021/jo00277a037
• 作为产物：
  描述：

  2,6-Dimethyl-phenylcyanat 在 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 N'-cyano(2,6-dimethylphenoxy)imidocarbonyl azide
  参考文献：
  名称：

  Functionalization of olefins by alkoximidoylnitrenes

  摘要：

  DOI：

  10.1021/jo00277a037

文献信息

• Functionalization of Phenyl Rings by Imidoylnitrenes. 2. Cycloaddition or Electrophilic Aromatic Substititution?
  作者：Hossein A. Dabbagh、Saied Ghaelee

  DOI：10.1021/jo951053f

  日期：1996.1.1

  The thermal decomposition of N'-[(cyanoaryl)oxy]imidoyl azides with various substituted benzenes (OCH3, NHCOCH3, C(CH3)(3), p-xylene, CH3, H, Cl, CO2CH3, NO2) has been studied in detail. With electron-rich aromatic nuclei, the addition of a nitrene yields a benzenonium ion (3) intermediate. Benzaziridine (1) and/or 3 intermediate is formed from benzene. Electron-poor aromatic nuclei generated only intermediate 1, in which no benzenonium diradical is formed. Intermediate 3 is stabilized by extended conjugation through an extra resonance structure. For electron-rich aromatic compounds at 65-120 degrees C, the thermodynamically-controlled products, N-arylisoureas ((Z)-NH-Ar), were produced in very high yield. Azepenes (the kinetically-controlled products) were detected by neither H-1-NMR nor a trapping experiment using tetracyanoethylene (TCNE). In the case of benzene 95% azepene was produced, which at 80 degrees C converted to isourea (k = 7.0 x 10(-5) s(-1)). The ortho/para ratio resembles that of electrophilic aromatic substitution reactions. The Hammett plot of log K-X/k(H) or log f(P) versus sigma(+)-values showed excellent correlation, with rho(+)-values of -2.80 and -3.10, respectively (poor correlation resulted with sigma-values). The Hammett rho(+)- or rho-values are inconsistent with a radical mechanism for these reactions.